


Refuge in Times of Trouble

by dopeysolo



Category: Supernatural
Genre: Alternate Universe, BAMF Women, Charlie Bradbury & Dean Winchester Friendship, Charlie Bradbury & Sam Winchester Friendship, Charlie Ships It, Dirty Talk, Eventual Relationships, Eventual Smut, F/M, Jo Harvelle & Dean Winchester Friendship, Jo Harvelle & Sam Winchester Friendship, Protective Charlie Bradbury, Protective Dean Winchester, Protective Jo Harvelle, Protective Sam Winchester, Reader & Charlie Bradbury Friendship, Reader & Jo Harvelle Friendship, protective Reader, sort of
Language: English
Status: Completed
Published: 2016-07-12
Updated: 2016-07-17
Packaged: 2018-07-23 12:28:18
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 5
Words: 14,921
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7463241
Author URL: https://archiveofourown.org/users/dopeysolo/pseuds/dopeysolo
Summary: <blockquote class="userstuff">
              <p>Reader is an experienced former military, current head of security for a software company. When something occurs that requires a different type of experience, she calls the Winchesters. Set in an alternative universe (sort of). The Winchesters are still hunters but Jo and Charlie work with the reader. The ladies are a couple of BAMF running a high tech security team.</p><p> </p><p>DISCLAIMER: All publicly recognizable characters, settings etc.. are the property of their respective owners. The original characters and plot are the property of the author. The author is in no way associated with the owners, creators amor producers of any media franchise. No copyright infringement is intended.</p>
            </blockquote>





	1. Cautious

The boys put Bobby on speaker as he explained, “My contact works as head of security at Micron Technology.” Sam interrupted Bobby, “Shit, Micron Tech? Are you serious”. Bobby laughed, “Serious as a heart attack, Sam”. Dean looked at Sam confused, which led Sam to explain, “Micron Tech is an American global corporation that produces many forms of semiconductor devices.” Dean continued to look at Sam confused. Sam sighed, “Big ass Tech Company worth about 16 billion dollars.” Dean perked up at that, “well, then Bobby, give us all you got”. Bobby laughed at the boys as he gave them the run down. “My contact is not sure what it is but she thinks something abnormal is going on. She is not to be messed with so Dean, please try and behave yourself.” Dean rolled his eyes at that and said, “Challenge accepted, Bobby”. Sam laughed as Bobby simply said, “idjits” and hung the phone up. 

The Winchesters pulled up to the gate at Micron Technologies. Dean rolled down the window when the guard asked who they were here to see, “We’re here to see y/n” The guard gave Dean a suspicious look when he picked up his phone to call it in. Dean whispered to Sam, “Man, I don’t know. Bobby didn’t give us much to go on and this guard is acting all shady. You sure this is just a tech company. I feel like we’re breaking in to the Pentagon.” Sam glared at Dean, and went back to reading. “It says here that she was in the Marine Corp, served 4 tours overseas and came back to take over their security. I can’t get much else on her.” Dean nodded, “keep looking, even with Bobby’s referral, I don’t like going in blind.” Finally the guard returned, and his whole demeanor changed, “Sorry to keep you waiting sir, Miss y/n is waiting for you at the front desk”. Dean nodded and drove off to park. Sam practically jumped out of the car and Dean laughed, “You’re like a kid on Christmas morning, it’s just a tech company Sammy.” Sam gave Dean his best bitch face and they both walked towards the door. 

They walked to the front desk where a security guard, clearly ex military or police and a petite blonde greeted them. Before they could speak, the blonde spoke up, “I presume, Dean and Sam Winchester?” the boys nodded, as the blonde leaned forward, “Hi, thanks for coming on short notice. I’m Jo, Deputy Head of Security and y/n’s right hand woman.” She went to the guard and told him to give them VIP visitor passes, registered as y/n’s consultants” The guard’s eyes went wide as he looked at Jo, “Y/n called in consultants?” Jo laughed, “Yes, even the mighty y/n needs assistances sometimes…” She took their badges and whispered as she handed them to the boys, “and by the look of them, hopefully they’ll assist her in some other areas too” Jo winked at Dean while he chucked and Sam turned a nice shade of red. 

The feisty blonde led the way to the elevator as both Sam and Dean looked around the building. It looked to be only 4 stories high, with security cameras everywhere and a lock on every door. Jo scanned her badge to get on the elevator. “Y/n arranged it so you have access basically everywhere except clearance level areas. Which is really only one room and y/n and I have access to it and since you’ll probably be with one of us at all times, it shouldn’t be a problem.” Sam took a chance to speak up, “Any idea why she called us in?” Jo looked at Dean and then Sam, “I do but I’ll let her explain.” Sam nodded as the elevator doors opened. Jo led the boys into a glass office, Sam looked all around observing the computers, and cameras everything was extremely high tech. He looked like a kid in a candy shop. 

Dean’s eyes focused on the woman in the office. His thoughts distracted him, ‘She was unlike any woman he’s ever seen. The first thing he noticed was how she carried herself, she oozed of strength with a subtle hint of femininity. She was fierce, he could tell by her tone of voice but there was something there, something that made him instantly want to take care of her, something about her, made him feel alive and refreshed. He was almost overwhelmed by her beauty and grace.’ Jo smirked and leaned over to him, “She’s something else, huh?” Dean simply nodded. “That woman that you are awkwardly gawking at, she is one of the best humans I know. She would literally take a bullet for her team. I’ve seen her do it. I’ve seen her throw knives across a room, silently with deadly precise accuracy. She has a mind like no other and that is saying a lot because I work with genius. I’ve also learned that if she has a hunch, its probably right. So, please hear her out”. Dean looked at Jo as Sam finally joined them in the office. You hung up your call and smiled at the Winchesters, “Thanks for coming so quickly and with not much information. Bobby helped me out years ago when a rogue vampire bothered a team of mine in Afghanistan. It was interesting finding out vampires not only exist but they exist in hellholes like a cave in Afghanistan. You come highly recommended by I man I trust so please have a seat and I’ll get right to the point.” 

With that the boys sat and Jo pressed a button causing the windows to black out. Sam looked around impressed by the technology that surrounded him but Dean focused solely on y/n. You blushed under the green eyed mans gazed, something about him that made you want to trust him, he made you feel calm which hasn’t happened in a long time. You both just looked at each other when Sam interrupted your thoughts, “Did you just blacken the windows?” Jo laughed, “Not many people appreciate that. I’m glad you noticed, I think its one of my favorite things to do.” Sam started to speak when y/n interrupted him, “Sam, I am sure Jo will be more than happy to show you two around and give you a sneak peak of some upcoming tech after the case is over.” Sam nodded when Dean spoke up, “Bobby said, you think something abnormal is going on. Why do you think its supernatural abnormal?” Y/n picked up a remote control, and a large tv screen turned on with a guys picture on it. “This is Dick Roman, as of a month ago, he was a low level employee in human resources. To this date, he has managed to move up the power ranks rather quickly, accidents keep happening to people and…Jo, do you want to tell this part, or shall I continue?” Jo rolled her eyes and waved y/n on. Smirking y/n continued, “What really confirmed my suspicions was when Jo described him as dreamy”. Dean and Sam looked confused, Jo smiled as she said, “I play for the other team.” Still holding their confused face, Jo smirked again, “To put it simply, I’m a lesbian”. Dean smirked and Sam’s eyes shot up. “So, you could see how I might grow suspicious plus I’ve never heard Jo describe a guy as dreamy” y/n said. Sam spoke up, “So, either this guy is the luckiest guy ever or something is going on.” 

Jo continued, “Y/n and I did some research, it sounds like he either sold his soul or he is a warlock which I like to point out that it is crazy that we are even having this conversation.” Y/n stood up, “Jo wasn’t with me during the vampire hunt so she is still getting used to the fact that things go bump in the night. I put together a file containing all the information I could gather about Mr. Roman, accident reports and any thing I thought would be pertinent. I arranged for you two to have an office right next to mine. You have access to computers, and an assistant to run to the library etc… I also set up payment for your services. Each day you will be compensated and you have adjoining rooms at the Grove Hotel, all rooms and meals are taken care of.” 

Sam stood up and shook your hand, “Thank you y/n. We will get to work right away.” Jo took Sam to their office as Dean lingered back. You both looked at each other, finally Dean spoke, “what does your gut say is happening?” You were shocked by his question, “As Jo stated, we think either he sold his soul or he is a warlock”. Dean eyed you again and you began to pause under his gaze. He raised his eyebrows at you and asked you again, “What does your gut say is happening?” You looked at him and sighed, “I think something bigger is going on. When you meet him, you’ll see that he is not a mastermind kind of guy. I think it’s bigger than we realize.” Dean smiled, “And that’s why you called in the big guns?” Y/n laughed at Dean, “Get to work Winchester, and let me know if you require anything”. He nodded and left your office. You sat down in a huff, shaking your head. Jo came in, “they are something else, huh?” You looked at Jo surprisingly, “No, no, not like that. I love my Charlie girl. BUT I know for a fact you need to get some and that Dean Winchester was eying you up.” You rolled your eyes at Jo, “Get to work, Joanna Beth”. Jo smirked, “Yes Ma’am”.


	2. Vigilant

**Summary for the Chapter:**

> Vigilant: Reader and Winchesters get to know each other. The Winchesters find out there's more to the story.

Dean and Sam settle into their office and get to reading. Well, Sam reads while Dean thinks. “There’s something she’s not telling us, Sammy” Dean says. Sam looks up from his file, “You think? She seems pretty straight forward, maybe we should ask her.” Dean shakes his head, “No man, I tried. I asked her. She thinks there is something more going on but she’s not sure.” Sam thinks about it, “Well, I guess we have to get to the bottom of it plus man, we actually get paid for this job!” Dean silently nods still contemplating your words, something was nagging at him, and something in your eyes told him there was something more. 

You found Jo on the third floor, doing some rounds and talking to people. Jo was the people person of your team. Part of her job, was talking to people, and getting a feel for the moral and atmosphere. You approached her as she was finishing her conversation. You nodded to the other employees and walked away with her. “You know it wouldn’t kill you to talk to them,” Jo whispered. You rolled your eyes at her comment. You both got into the elevator, “Are you going to tell them?” Jo looked at you with one eyebrow raised. “It’s not pertinent to the investigation,” you calmly answered. “Are you kidding me? You’re getting death threats and you don’t think it would be pertinent?” Jo exclaims. You sighed, tired of having the same conversation with Jo, “the timelines do not match. Dick Roman’s behavior started a month ago, my first threat was a week ago. We did the research and they are not relevant”. Jo groaned, “Ugh y/n, stop being a stubborn ass and tell them”. “Absolutely not, I am not some damsel in distress so quit bringing it up Joann”. Dean laughed, freezing you in place, afraid of what he over heard… He stepped forward and said, “Joann? I didn’t peg you as a Joann and as for you being a ‘damsel in distress’ any fool with eyes knows you are not to be messed with.” You blushed at his words and Jo stood there blinking, “Y/n did you just blush? Hold the damn phone, I’ve never seen her blush. Dean Winchester, I think you and your beautiful face broke my cold hearted boss!” Now it was your turn to stand there blinking, unsure what to say to Jo’s bluntness, when the elevator bell dinged and the lunch cart was brought in to the offices. “Saved by the bell,” you uncomfortably laughed as you told Sam to come out to eat. 

While you were eating, your assistant came in and said, “Ms. Y/n, don’t forget the team leader getaway is this weekend. Should I confirm your reservation?” Jo started to laugh, as you simply said, “Shit”. Dean and Sam looked up from their food, curious as to what has you pissed off and Jo laughing. Your assistant stood there awkwardly, as you said, “Change the reservations to JoAnn Harvelle and Charlie Bradbury please.” Jo abrutely stood up, “Ahhh hell no. I’m not going to that thing again. You’ve made me go every year for the past two years”. You simply looked at Jo as she rolled her eyes and sat down, “Fine, fine. I’ll call Charlie”. Your assistant quickly walked away. You looked across the table to see Dean and Sam just staring at you and Jo. 

Jo took the time to explain, “Every year the head honchos host a team leader getaway. It is supposed to encourage unity and help the bosses’ to be better leaders but really all it is, is a booze fest, with a lot of sex and not necessarily with whom you came with. Y/n hates that shit, she is unable to be a kiss ass and if I remember correctly that last time you went, you held a knife to a drunk mans throat.” You laughed, “That story has been wildly taken out of context but yes, I loathe those things, plus you are better with people”. Jo rolled her eyes, “don’t try and compliment me, I already said I would go so shut it.” Dean laughed, “that sounds like some getaway, I would love to hear your version of the knife story”, as he winked at you. 

“No way man, she’ll just downplay it. You see what happen was the former CEO’s husband got so drunk which led to him being handsy. He sure picked the wrong woman to be handsy with.” Jo started to laugh as she told the story. “Y/n made Charlie and I go with her, it was the first time we went and man, were we shocked. A couple people hit on us but we were able to navigate away from that but for some unknown reason this guy latched on to y/n. He kept pestering her, at first it was funny, but it soon went from funny to annoying. I knew if I thought it was annoying, y/n thought it was infuriating so Charlie and I played bouncer the first two days. You have to understand, that we played bouncer for his sake not for y/n. We wouldn’t leave her side, and every time he came around, we controlled the conversation. He seemed to lose interest the last day, so we began to relax a little. Y/n was on edge the whole weekend because she hates socializing with those types of people, She says she would rather be tortured than thrown in a room full of privilege, opportunist back stabbing crooks. Anyway, it’s the last day and everyone was off making the best of their day. The three of us decide to go swimming, well seeing y/n in a bathing suit must have been the last straw because that man was all over her. She finally had enough and out of nowhere she pulls a knife and shoves him against the wall. The man actually looked excited until he felt the knife slowly nicking his neck. Charlie and I bolted to her side, pulling her off of him as his wife, our boss came over, she apologized for her husbands behavior and quickly left.” 

You shifted uncomfortably after the story, “Jo tells it a tad more dramatic than it was”. Jo gave you a bitch face, “Oh please, that is exactly how it happened, want me to call Charlie and have her tell it?” You stood up, “Ok, that is enough, I’m sure we still have work to do.” Jo shook her head as she followed you leaving Sam and Dean still holding their sandwiches. “They are something else, huh?” Sam whispered. Dean laughed, “They sure are”. 

Around 7:00pm, you went into the Winchesters office to see if they were still there and sure enough they were. You watched them work for a little bit, you watched as Sam read to Dean and Dean put pieces of paper in order. You cleared your throat to get their attention. Both boys looked at you and smiled. You walked in and said, “I’m calling it a night. I’m headed to the Grove Hotel, if you want to follow me.” They nodded and gathered their stuff. Jo met you three at the elevator, “Did you get a room at the hotel, y/n?” You simply nodded yes. Dean asked, “Why are you staying at a hotel y/n?” Jo looked at you, “Yeah, why are you staying at a hotel?” You glared at Jo, as you smiled and said, “My house is being fumigated”. Jo rolled her eyes as she walked into the elevator. The boys noticed the exchange in dialogue but decided not to question it. 

You all walked out to the parking lot. Dean and Sam walked to the Impala while Jo and you said your goodnights. Dean pulled up and you eyed his car, “She’s a beauty, Winchester”. Dean beamed with pride, “Where’s your ride y/n?” You nodded and walked over to an all black Ducati Diavel. You pulled on your leather jacket and helmet as you started your bike up. Dean’s mouth fell open as he watched you saddle your bike and start it up. Sam chucked at his brother, “Dean, close your mouth and start driving”. 

They followed you to the Grove Hotel. The boys got out and looked at the luxury hotel. “Well, Sammy, this might be a little better than what we are used to”. The boys gathered their stuff as you walked over to them. “The rooms are in the company’s name, figured you guys didn’t want your name documented” You winked at Dean and the three of you walked in. You checked in and got into the elevator. Your rooms were on the same floor so you walked together. Dean stopped you and said, “We’re going to get something to eat, if you’d like to join us?” You smiled, “Thanks but I have a protein shake and I think I’m going to swim some laps.” Dean nodded as he brain pictured you in a swimming suit. The boys left as you went into your room. You quickly made your shake, as you got ready for the next day. You checked in on the team you assigned to look in to the threats. Charlie answered, “Hey good looking! Heard you had an interesting day?” You smiled at her enthusiasm; she had a way of making her happiness contagious. It was near impossible to be in a bad mood when she was around. “Any new developments on the notes, Charlie?” you asked. Ever the professional Charlie said, “Not yet, I am still analyzing everything. I should have a report by tomorrow. Jo said you got a room, so rest easy. I stationed two man teams one at your house and two teams at the hotel. Just press your special button and they will come to your location.” You thanked her and hung up. You were beat but you knew if you didn’t get some exercise in, you’d be grumpy. You changed and made your way to the hotel pool. 

You did your laps and saw it was nearly 9:30pm so you decided to head back to your room. When you started to climb out of the pool, you heard footsteps and quickly turned to see a smirking Dean Winchester. “Well, hot damn, now I understand why that man had a breakdown at the sight of you in a bathing suit.” You hurriedly wrapped your towel around yourself as Dean approached, standing directly in front of you as he said, “Princess, covering up that body should be considered a crime.” You looked up at Dean and laughed, like whole-heartedly laughed, “First, don’t call me princess, pretty sure I could kill you with my bare hands and second, do those type of lines work?” Dean looks down at you and smiles. A real smile, the kind of smile that seems so genuinely sweet with just the right touch of shyness that unexpectedly causes warmth to rush through your body causing you to shiver. He sees you shiver and puts his hands on your arms, he rubs them attempting to warm you up as he says, “First, surprisingly those lines do work and second, you might be able to kill me with your bare hands but I’d put up a fight that you’d remember forever”. You gulped at his nearness and intenseness in his eyes. You two just stayed there for a minute, when you shivered again but this time from being cold. Dean put his hand on your back and ushered you to the elevator, “Come on, let’s get you upstairs”. You got in the elevator with two men in suits. Dean instinctively moved closer to you. You smiled at his actions, usually that type of Neanderthal behavior was unacceptable but for some reason when Dean Winchester did it, you had quite the opposite reaction, in fact you were thinking maybe a cold shower tonight to get your mind off of a certain green eyed hunter. 

The elevator bell dinged and you went to get off when a hand not belonging to Dean Winchester grabbed you. Before you had time to speak, Dean punched the man and he was down in seconds. “STOP” you shouted causing Dean to freeze. You looked down at the unconscious man and looked back at Dean. The other man in the elevator stood frozen. You sighed, “Charlie assigned you?” The man nodded yes. “Fine, take your partner, wake him up. Next time you are assigned to follow a client, don’t make contact with them unless they are in trouble, you are trained to blend in not get knocked out by a civilian in the elevator.” “Yes Ma’am” is all the man gets out before the elevator dings again. You and Dean step out. “Quite a punch you have there, Dean”. He continues to look at you. Sam hearing the commotion opens his door to see you and Dean facing off in the hallway. You shifted uncomfortably, just nod and say goodnight to the boys. As you turn you hear Dean say, “Now wait just a damn minute princess”. You turn to look at him and he gets dangerously close, as he practically growls, “I know you’re used to being the boss but when we are called into a case, we need to know everything and that back there was a definite need to know. So, either Sam and I will follow you to your room or you can sit your pretty ass in our room. Your choice, princess.” You glared at Dean and turned towards your room, you motioned to Sam to follow. 

You got to your room and silently opened the door. The boys came in and sat down on the couch. Dean began to speak when you cut him off. “I’m going to shower and change then we can chat”. The boys nodded and you went to the bathroom. You took a relatively quick shower and changed into a tank and shorts. You came out to see Sam and Dean still sitting on the couch. They both glanced at you as you walked out. You felt Dean’s eyes look you up and down but then he settled on your face and he still looked pissed. You sighed, as you sat down in the chair across from them. “A week ago, I received a death threat and two days ago, I received another one. I have a team led by Charlie working on it. In the elevator, you met part of the team assigned to my security.” Dean continued to look at you as Sam spoke, “Y/n you really should have told us earlier. It might be connected to Dick Roman”. You shook your head, “No, no we had the cases looked at to find any connections, there are no connections between the two therefore irrelevant information for your case.” Sam began to speak when Dean cut him off, his voice was rough, “Y/n, we need to see the threats and you need to tell us everything, where you found them, when you found them and any events leading up to the notes.” You stood up, “Listen, its not that big of a deal.” Dean stood up and marched over to you, “From now on, I will tell you what is or isn’t a big deal. We can’t do our job if you don’t cooperate.” Sam watched wide-eyed as these two larger than life personalities go head to head. You glared at Dean, no one has ever spoken to you like he does, you weren’t sure if you wanted to knock him out or push him against the wall and fuck him. “Holy hell y/n, get ahold of yourself” you thought. 

Dean glared at you until you looked back at him, “I’ll have Charlie send you the case file. Now if you wouldn’t mind, I would like to get some sleep.” Sam stood up to leave while Dean stood there. “Night Sammy” he said and Sam once again stood there watching the events unfold. “What do you mean, ‘night Sammy’, Dean? I want to go to sleep therefore you need to leave too” You stared at him waiting for him to move but he didn’t budge. “Ummm, I’m going back to my room. I’ll look at the case file as soon as Charlie sends it”. With that Sam left you and Dean alone. You both stood toe to toe glaring at each other. You broke the silence; “You know I probably could physically remove you from this room.” Dean smirked, “You can try but I ain’t going anywhere, princess”. You stepped forward, “Dean Winchester, get the hell out of my room”. He continued to smirk as he stepped around you, plopping himself on your bed. “As I recall, I now get to decide what is or isn’t a big deal. You’re my client, my client is being threatened therefore you need better security than those two bumbling fuck ups in the elevator. Plus I know you know how to fight humans but what happens if it is something supernatural? In your training do you know how to fight off a ghost, changeling or a demon?” You sighed; fucking Dean Winchester had a point, damn him and his logic. You turned off the overhead light, leaving just the night stand on but enough light to see Dean kick off his boots, take off his jeans and flannel leaving him in a t-shirt and boxers. “Dear Jesus, this will be a long night,” you thought. Turning off the light, Dean leans over and whispers, “No funny business, y/n.” You shook your head as you heard him chuckle at his own joke. 

Your alarm woke you up, you quickly turned it off groaning, you slept wonderfully, and you haven’t had that much sleep in years. You turned over only to be greeted by twinkling green eyes. “Morning Princess, How’d you sleep?” he murmured. You squinted your eyes, “I slept just like normal, thank you”. You would never give him the satisfaction of knowing how well you slept. “Well, I slept great, I haven’t slept that great in a long time”, he said as he sat up. You just glared at him and silently got up to get ready for the day. Dean went to his room, to shower and dress and everyone met out in the hallway. You pulled out your phone and started answering e-mails and texts when Dean suddenly covered your phone, you looked up at him as he smirked, “No work yet, what’s for breakfast?” You shook your head and put your phone in your back pocket. “I get breakfast served at the office. You two are welcome to join me otherwise, there’s a diner down the street.” Dean eyes lite up at the thought of a diner when your phone rang. You went to pick it up and Dean just shook your head at him. Ignoring him you answered, “Yes, Jo?” You quietly listened at she spoke; the Winchesters watching your facial expressions go from calm to annoyed in seconds. You told Jo that you’ll meet her in the office in 10 and hung up. You silently walk to the elevator with the Winchesters in tow. Dean watched as you tried to make sense of whatever Jo told you. It was as if he could see your brain working and trying to figure out the puzzle. The elevator doors opened breaking your train of thought. You glanced up and saw the rain. With a sigh, you looked over to the Winchesters, “Do you mind driving me to the office?” Dean and Sam nodded and you walked towards the exit. Much to Dean’s chagrin, he had to valet baby so they waited for his precious to be pulled up. Sam finally brought up the phone call, “y/n, anything you need to share with us?” You looked up at Sam and smiled. “Yes” you said calmly as you climbed into the back seat. Both boys shook their heads and follow suit. 

As soon as Dean pulled away, you sat forward and began to explain, “Jo called to tell me that the list of attendees for the retreat has changed. I beginning to see a pattern and I do believe I spoke to quickly regarding the connections between my threats and Dick Roman. The former CEO and her husband are now included on the guest list as well as Dick Roman himself.” You sighed and sat back. Sam turned to you, “Ok, so what pattern do you see?” You looked at Dean in the mirror, “I am the reason she is a former CEO”. Dean muttered a “damn it y/n” and you quickly continued your story. “I knew something fishy was going on with her so I quietly started to look into her actions. I gathered more and more data until I had enough indisputable proof to go before the board. She was completely blindsided and quickly voted off the board. Naturally she blamed me for her actions. The board elected the now CEO, who from what I can tell a decent man and boss. The fact that he invited her to this event is quite suspicious.” Dean pulled into the parking lot to see Jo waiting outside with an umbrella as well as two others for the Winchesters. Jo handed the umbrellas to the boys as she waited for you to emerge from the back seat. “Did you fill them in?” Jo asked and you nodded walking towards the doors. You greeted the security guard and walked towards the elevator. Jo and Sam talked about the elevators computer interface while Dean watched you process the new information. The doors opened and you quickly called over your assistant, “Change the retreat names back to myself and guest.” Your assistant looked up and every one else stopped in their tracks, “No need for names, just add a guest to my reservation”. Your assistant quickly wrote down everything down and hurried off. You motioned to your group to go into your office. Jo blackened the windows and every one sat. 

“Dean and I will go on the retreat. You, Charlie and Sam will book a hotel within a 5-mile distance so you are all easily accessible. I believe our former CEO is out for revenge, taking out the company as well as myself. For some reason she is using Dick Roman whether to take over as CEO and use him as a puppet or for some other unknown reason. All I know is the current CEO wouldn’t stand for it so something is going on and I need to be there.” Looking over to Dean you smiled sweetly, “I mean, if that’s ok with you Mr. Winchester?” Dean rolled his eyes, “Yeah, it sounds good although we still have no idea what we are dealing with.” Jo glanced back and forth between you and Dean, “I feel like I missed something. Did I miss something? What happened, Sam?” Sam looked at Jo and laughed, “You missed something all right”. Both you and Dean glanced over towards Sam and Jo and smirked. Dean got up, “Sammy and I will rule out every thing we can so we can go somewhat prepared, in the meantime, princess, you don’t go anywhere without Sam or I, is that clear?” You scowled at his order but smirked and said, “Yes Sir” as you mock saluted him. Jo stood up, “Ok, I definitely missed something, Sam, my boy, you need to fill me in!”


	3. Reactive

**Summary for the Chapter:**

> Reactive: Reader and Dean prep for a weekend away

Jo gave Sam a tour of the building while introducing him to certain people as a new member of the security team. Jo teased him mercilessly as the women practically swooned when they met him. Sam just blushed at her accusations. Dean didn’t leave the office and would periodically check on you. You wanted to finish some paperwork considering you would be out of the office for the next few days. Needing a break, you got up and went into Dean’s makeshift office. He stood as you entered. You slowly approached him, unsure how to ask him but you started, “I was thinking about what you said and you’re right, I can fight humans but I was wondering if you’d give me some tips on how to fight something supernatural?” You took a chance to look at Dean; you could see that he understood how hard it was for you to ask for help so he did his best to encourage you. You smiled at his sweetness, “I know we don’t know what we are up against but maybe if you gave me your best guesses I wouldn’t feel so unprepared. I hate feeling unprepared. I like control.” Dean cut off your nervous ramble, “Sometimes, actually most time in hunting, things don’t go to plan. You know what that is like considering your multiple combat tours.” You nodded impressed he did his research. He took a step forward, “you have to be prepared for anything” as he swung at you, you quickly dodged his punch. He smiled at your swiftness as he continued to circle you, “For instances, Demons look like human and fight basically like human, but they have supernatural strength and can ultimately take control of your body.” He quickly launched two punches and tried to trip you but you successfully sidestepped his movements. He nodded, impressed that you were still standing. Like a predator circling his prey, he continued, “witches are nasty creatures, usually you have to find a hex bag and destroy it while fending off curses, in the end a bullet or knife usually do the trick but you have to be careful because they are clever ones, always up to something” and just as he said that, he bombarded you with punches and kicks, you two fought, blocking what you could, throwing punches back and forth, finally, you managed to trip him, and force him to the floor, straddling him. Breathing heavily, you and Dean looked at each other. He gently put his hands on your hips, “Well, Princess, no doubt about your fighting skills. It’s a shame you are wasting it away up here in your ivory tower”. Before you could answer, Charlie interrupted, “Jo is going to love this” and she quickly took a picture. You glanced back at Charlie only to be quickly thrown to the ground with Dean Winchester on top of you. Your eyes widen as he leaned down and whispered, “Remember they are always up to something”. Charlie murmured, ‘Sweet baby Jesus, that’s hot”. Dean jumped up and held a hand out for you to take it. Unable to really find words, Dean grinned, “Nice lesson y/n. Keep up the good work.” as he slapped your ass and walked towards his desk. You eyes went wide especially when you saw Sam, Jo and Charlie in the entrance of the door. “I keep missing things” Jo exclaimed. Charlie grinned and showed them her phone. Their eyes shot back to you and Dean, Sam and Jo smiling ear to ear. You rolled your eyes walking back to your office. 

You finished your paperwork and began to pack up. Jo came in your office and told you that she was able to book a room 1.2 miles away from the resort. She handed you a file with the blueprints, room locations and itinerary. As well as anything else she felt pertinent. The Winchesters walked in as you picked up her file to put away when something fell out. Dean bent down to pick it up when he began to chuckle. You looked at him puzzled and then you saw what he was holding in your hands. “Charlie gave me a file as well, all things necessary to the case including one of these”. You looked down and saw a condom package in his hand. You looked back at Jo who conveniently left the room with Sam. You muttered, “I’m going to kill them”. Dean snickered, “Relax Princess, they’re just messing with you”. You hated that he was so nonchalant so you decided to mess with him. You leaned forward, giving him ample view of your cleavage, “Oh I know they’re just messing with me, they know me better than that. I need at least three condoms for a night”. Dean visibly gulped as you smirked and walked away. 

Charlie, Sam and Jo packed up the van with all the necessary equipment while you and Dean packed. Jo pulled up as you guys finished loading the impala. Charlie jumped out and handed you something. You put it in your ear as Dean watched. “What are you doing y/n?” Dean asked. You held out a small device and said, “These are comms, put them in your ear that way every one can hear what is going on at all times. It helps with the mission to stay in contact. Plus Charlie here, will have access to the resort’s network when she sets up so she can give us a heads up when we are walking in to different rooms.” Dean grabbed the device as Charlie showed him how to use it. After every one tested the equipment, you guys loaded up and started to the drive to the resort. 

The drive to the resort was spent figuring out Dean’s cover story. His name was Dean Smith, he works in private security, and you met when Dean consulted for you. Charlie created an online cover story, creating a linkin page and a website on the company he works for. You figured to keep close to the truth so it would be difficult to mess up. As you pulled up to the resort, Dean glanced over as you took a deep breath. Gently he squeezed your hand, you smiled, “Funny as this may seem, I’m not nervous about fighting a monster but more socializing with these people”. He let go of your hand as he pulled up to the valet. “Yeah, but at least you won’t be alone. I won’t leave your side” Dean winked at you and put his baby in park. The valet opened your door and immediately stood at attention as you got out. “It is imperative that this car is in the front where I can see it at all times. Is that clear?” The valet nodded, “Of course, Ms. y/n”. Dean got your bags out and put his hand on your back, leaning in he whispered, “Smart thinking. That car has all the weapons we will need to basically fight anything”. 

Before you could respond, you both heard Charlie’s voice, Dean jumping a little because he forgot about the comm system. “Ok guys, every one is pretty much here. As soon as you enter, you’ll be greeted by Mr. Mark Durcan, the CEO and his wife, Belinda.” Dean looked down at you, “Ready Princess?” You took another deep breath and walked in. 

The CEO walked right up to you guys, greeting you excitedly, Dean never removed his hand from your back giving you the support you needed. “Mr. Durcan, Belinda, this is Mr. Dean Smith, he’ll be my guest this weekend.” Mr. Durcan and Belinda looked at Dean and smiled but you noticed how Belinda took all of Dean in. Frowning at her behavior, you stepped closer to him as put your hand on his chest, “My boyfriend” causing Belinda to immediately stop gawking at him. You heard Jo through the comms, “this just got interesting”. Dean snickered as he leaned down and kissed your forehead. “Well, aren’t you two just adorable. I must say y/n, I was surprised to see a guest listed on your reservation. You’re usually so private”. Dean spoke up this time, “Mr. Durcan, that’s my fault. You see I decided to surprise my girl this weekend by popping in for a visit. So, we decided to combine some business with pleasure… if you know what I mean…” You turned bright red at his innuendo as Mr. Durcan laughed out loud and Belinda pouted. All the while you could hear the laughter through the comms and Jo reminding you two to turn off the comm links if anything pleasurable happens. 

You checked in, got your room keys and headed towards the elevator. As soon the doors closed, you turned to Dean, “Please remember that I have to work with these people after you leave and I have a certain reputation...” Dean interrupted your speech, “I know, I know…you have a position of authority here, but if we’re going to get any information out of these people- someone has to play the good cop.” You looked at him confused as he continued to explain, “Good cop” he pointed to himself and “bad cop” he pointed to you. “These people know what you are capable of but you’re not exactly approachable so they need someone to approach if they have information.” You contemplated his words when Jo broke the silence; “He’s right y/n. just go with it”. You nodded as the elevator doors opened. 

You opened the door to your room. It was a spacious suite with a king size bed and luxury bathroom equipped with a huge walk in shower and Jacuzzi tub. The room was centrally located above the pool and recreation area where most of the outdoor “meetings” were held. Giving you and Dean a perfect window to observe. As you and Dean unpacked, Charlie explained the locations of the rooms and where the others are located. Lastly, Charlie went over the schedule, you groaned as she reminded you that tonight’s dinner is in the main hall, which meant dress up. You knew it was a perfect event to get people talking especially with alcohol but you still hated the idea. You told Dean that you’d take a shower first to start the process of getting ready. You removed your shoes, socks and earpiece and went into the bathroom. Essentially leaving Dean alone. 

As he sat back in his chair, Charlie began to speak, “Dean, yours and y/n dress clothes will be at your room in about 15 minutes.” Dean interrupted, “Charlie my suit, is hanging up. I’m looking at it now”. Now it was Jo’s turn to talk, “Yea, about that. I took the liberty to order you a new suit. These people are terrible and they would pick you apart with your suit. If it makes you feel any better, I have to order her dress as well. I know y/n could care less. Hell, she’d go in jeans and a t-shirt if she could.” Dean perked up at that, “Really? She always seems so put together.” Jo and Charlie both laughed at that as Jo spoke, “She’s put together all right but hates the idea of dressing to impress other people. Give her jeans and a t-shirt any day. Remember she is used to being in fatigues.” Dean liked the idea of seeing you relaxed and in jeans. “Dean” Sam said through the comms, “It looks like we are dealing with demons but I don’t understand why they would they be so focused on destroying a company and y/n”. Dean sighed, “I don’t know man, its sort of unusual activity for demons but keep looking. At least we have an idea of what we’re up against. Oh and tell the girls about the anti-possession symbol.” Sam agreed and asked, “What about y/n?” Dean snickered, “she already has one”. Jo chimed in, “She does? Where? I’ve never seen her with a mark on her body?” Dean chucked, “Trust me, she has one.” Jo rolled her eyes, “I feel like I’m missing a story here.” Sam spoke up, “Dean has excellent observation skills when it comes to the female body”. “Hey, so do I!” exclaimed Jo. Dean interrupted, “Guys, calm down, I saw her in a bathing suit, she has one discreetly hidden. To the untrained eye, it probably just looks like a birthmark but I know what it looks like.” Jo went to ask more questions, when Charlie spoke up, “Listen Dean, you’re clothes are on their way up. The former CEO’s husband just found out that y/n’s here and he seems quite excited to see her again. Under no circumstances do you leave her alone especially with him near. She will not hesitate to harm him. If you need back up, you say the word and we will be there in two minutes. Don’t worry we timed it.” The door knocked as he heard y/n turn the shower off. Dean assured the team, “ I don’t want that creep near her. I wont let her leave my sight.” Jo laughed, “Yeah I bet you won’t”. 

Dean was closing the door as you opened the bathroom door. You came out in a big fluffy bathrobe and your hair tucked away in a towel. You sighed and plopped down on the chair, “Best shower ever. I forgot how wonderful they were. I feel so relaxed.” You looked over to Dean as he hung the dry cleaning bags up. “Are those our clothes for tonight?” you asked. Dean nodded, “Yep, Charlie sent them over. I guess I’ll head to the bathroom as you start to get ready?” You smiled, “Enjoy, take your time.” As Dean headed in to the bathroom, you started getting ready. 

You had all your undergarments on including your garter and holster for your knives. Your hair and make up was done, you just needed to put your dress on. You heard Dean turn the shower off a few minutes ago so you assumed he was just getting dressed. The door opened and Dean stepped out in an undershirt and tight boxers. You tried your hardest not to stare but damn, did the man look good in everything. He grabbed his suit and put on the pants. Finally he looked at you, “See something you like, princess?” Jo laughed in the comm, “Please tell me he is in a towel. Y/n? Close your mouth y/n.” You quickly muttered a “shut up Jo”. You got up and went to your dress. You pulled off the plastic from the dry cleaner, “Son of a bitch. Jo, this is not a dress” you said rather annoyed. Dean managed to put his shirt on and walked over. Looking at the dress, he smiled, “I whole heartedly approve of this dress. Well done, Jo” You glared at him, “Yeah, well you’re not the one that has to walk around basically naked!” Jo defended her dress choice, “Oh come on, y/n, you might as well have some fun this weekend. You are gorgeous, its time you flaunt it. Plus it might get some information out of some people.” You groaned as you pulled it off the hanger. “Turn around Winchester” you demanded. Dean obeyed as he listened to you slip the simple black halter-top, neck plunging mini dress on. You cleared your throat, “Um Dean, can you fix the back so its even, please” Dean didn’t even hesitate before he was behind you, straightening what needed to be straightened. He stood back as you turned; his eyes went up and down your body when he stopped at your face. He stepped forward; your eyes never left his, he leaned over to your ear without the comm and whispered, “You look exquisite” and kissed your cheek. You smiled as Jo said, “we couldn’t hear, what’d he say?” Charlie nudged Jo, “there are some things that we don’t need to hear. Would you want every one to hear what we talk about?” Jo’s eyes widen and then she smirked. Dean opened the door and you two walked out of the room, ready to face this mission head on. 

You two arrived in the main hall as every one was already sipping on their cocktails and talking. You walked in with Dean in tow, both of you looking around the room and taking every thing in. Mr. Durcan was the first to approach you. He smiled and greeted both you and Dean. You made idle chic chat when you saw the former CEO. You immediately stiffened; Dean put his hand on your bare back, making soothing circles while you continued to talk to your boss. You visibly relaxed under his touch when you saw her approaching with her ass of a husband. Before she got closer, you flat out asked Mr. Durcan, “Sir, I realize this might be overstepping but Why is she here?”. Mr. Durcan rubbed his head, and stuttered a little before answering rather robotically, “Isn’t it time to bury the hatchet?” You squinted at him, “I don’t understand why you didn’t tell your head of security that you were inviting a safety risk?” He blankly stared at you and repeated himself, “Isn’t it time to bury the hatchet?”. You turned and looked at Dean and he nodded. Before you could escape, the former CEO and husband approached you. 

Dean instinctively moved closer to you, still rubbing soothing circles on your bare back. You suddenly felt very aware of how much skin you were revealing and cringed at the thought of her husband looking at you. As if realizing your internally struggle, Dean leaned in and whispered, “Princess, you could be wearing a potato sack and that creep will still undress you with his eyes. You look beautiful.” And he leaned down and kissed your forehead. “Well, well, well, I must say it’s lovely to see you so happy y/n.” the former CEO said. You glared at her and didn’t even glance at her husband. “Patricia, we were just talking about you. Dean, this is Patricia, the former CEO of the company, she was fired because she was caught stealing and this is her husband, Paul, he is irrelevant.” Dean choked on his drink, as he looked at you, holding in his laughter, you smirked, “Patricia and Paul this is Dean Smith, former black ops turned private security…” you finally made eye contact with Paul as you continued, “and lover”. Dean squeezed you tighter, then held out his hand, and said, “Nice to meet you Patricia and Paul” Neither of them shook his hand and he just shrugged and let it fall. You and Dean just looked at Patricia and Paul while they scowled at you. Finally Patricia spoke up, “Well, I was hoping to put the past behind us but I guess I was wrong.” You leaned in as you simply said, “You were very wrong”. She turned in a huff calling Paul to come with her. However Paul grinned at you, “I knew you were a feisty one” as he licked his lips. Now it was Dean’s turn to lean in, “Careful bud, that’s my girlfriend you’re speaking to and I don't share”. Paul seemed unfazed by his threat and turned and winked at you before going after his wife. 

Charlie broke your silence, “Damn, that awesome!” she exclaimed. Jo and Sam were laughing out loud. Dean smiled at you, “I agree, that was pretty badass y/n.” You blushed, “You weren’t too shabby yourself” as you nudged him. Out of the corner of your eye, you saw Patricia and Paul leave through separate doors, “Ok, breaks over. They are on the move.” You heard Charlie typing away as you gave your instructions. “Dean take Paul and I’ll follow Patricia” you started to move when Dean’s hand grabbed yours, glancing down you frowned, as he said, “Not so fast Princess, I don’t like the idea of separating.” Your facial expressions soften, leaning in you kissed his cheek, “lets go get us some bad guys, then maybe you can help me get out of this dress”. He shook his head but let you go. He watched as you went out of the door. Dean quickly went and followed Paul.


	4. Aware

**Summary for the Chapter:**

> Something supernatural is happening but will they solve it before the reader gets herself in to trouble

You walked down the hallway; keeping a safe distance from Patricia, careful not to make much noise, if she was supernatural, you assumed she could sense your presence. Suddenly you heard voices; you stayed behind a wall, listening to a conversation between Patricia, Dick and someone else. Patricia clearly nervous whispered, ‘She brought a Winchester. I knew we should’ve just cut and run. This is pushing it.” Dick chimed in, “A Winchester?! Just the one or both of them?” Patricia visibly shaken, “Does it matter? Plus you know if there is one, the other is near by!” You couldn’t help but smile; these Winchesters certainly have a reputation. The other voice you couldn’t pin point spoke up, “Enough, we came this far, we’re not going to stop just because some hunters are thrown into the plan. We go forward. I’ll take care the Winchesters and you two follow through with the plan.” You heard movement and you silently and quickly moved towards the main hall. 

Casually walking in to the main hall, you gracefully picked up a champagne flute, blending into the crowd, you whispered, “Dean?” You felt a hand on your back and his warm breathe on your neck, “Right here, Princess”. You smiled and turned to face him. His green eyes sparkled as he took your flute and placed it on a passing waiters tray, “Dance?” You nodded and he led you out to the dance floor. A beautiful slow song began to flow through the speakers as you and Dean turned to face each other. He stepped closer; running his hands down your bare arms, not slow but fast. His hands felt electric, basically jump starting your heart. He smiled putting his hands on your waist pulling you closer. You wrapped your arms around his neck and began to sway to the beat. You two didn’t break eye contact; his eyes seemed to be filled with so much emotion. You felt your heart beat rapidity, it was like his gaze was bringing you back to life, reviving what was lost and restoring what was shattered. 

The intense stare was broken by Charlie’s voice, “Well?” You blinked and smiled at Dean as you leaned in to dance closer and whisper in his ear. “Three voices, 2 male and 1 female: Patricia, Dick and unknown subject. Patricia recognized Dean and two of them seemed nervous that a Winchester was here.” Dean pulled you tighter, causing you to feel his solid body, and he whispered, “They should be nervous”. You smirked and continued; “Dick and Patricia were instructed to go on with the plan while the unknown subject was going to take care of the Winchesters.” Sam voice suddenly came through the comm, “I’ll search the footage to see if we can get a face of the unknown and go from there” Jo piped in, “We did some more digging, it looks like you were right y/n, Dick Roman’s gunning for the CEO position. Charlie tracing Mr. Durcan to find out the source of his odd behavior, in the meantime, you two keep your eyes opened and focused.” Dean smirked, “she’s a bit bossy, isn’t she” Charlie murmured, “You have no idea” Both you and Dean laughed. 

You went about the room chatting with different people while keeping an eye on the subjects. You wanted Dean to meet Dick Roman but he kept his distance from you two. Most of the people you talked to felt a little uneasy with Patricia and Paul’s presence but they didn’t want to say anything to upset Mr. Durcan. In fact one board member pulled you aside to express his displeasure and lack of faith in the CEO, “I’m beginning to question Mr. Durcan’s leadership abilities, if he invites the likes of her to our leadership retreats after what she costs us…I am a little nervous about her being here.” You nodded along and listened to his complaints in the mean time Charlie seemed to be on to something with the CEO’s strange behavior. “He doesn’t seemed possessed, it has to be something else controlling him.” She sighed. Sam pitched in, “There’s only one way to find out, Dean?” Politely Dean excused himself and went to find Mr. Durcan. Dean found the poor guy rubbing his head. He went over and put his hand on Mr. Durcan’s back, “Hey man, are you ok? You don’t look so good.” Mr. Durcan reluctantly stood upright, “I’m ok, I just haven’t been feeling myself these last few days.” Dean perked up at that but just to be sure, he leaned closer and whispered, “Christo”. The CEO just stared at him. Dean smiled awkwardly, “So the last few days you’ve been sick?” Mr. Durcan nodded, “Yeah, I’ve been getting awful headaches.” Someone came over and began speaking to the CEO. Dean lingered near him and murmered, “Not demon”. Sam calmly said, “Demons have used curses before, maybe he has a cursed object on him?” Dean rolled his eyes, “How the hell am I going to find a curse object?” 

You listened and watched Dean as he chatted with Mr. Durcan. You could hear every thing Dean and Sam were saying but you also had to listen to this board member. Finally he stopped talking so you took the opportunity to assure him that all safety procedures and protocols are being followed. “As far as Mr. Durcan, I wouldn’t count the man out. He’s a good guy. I’m sure he has his reasons for having them here.” He seemed satisfied with your answer and left. 

You turned to see Dean still near the CEO so you made your way over to him. You nodded to Dean as you went towards the CEO, Dean looked confused until you spoke and his confusion turned to shocked, “Excuse Mr. Durcan, I know this is going to sound weird but are you wearing something that you recently got, or something that you had cleaned out side of your home like a watch or ring?” Mr. Durcan looks confused for a second and then nodded, “actually yes, I was talking to a friend and I noticed his beautiful watch. He told me that he would get me one. I paid for it, I promise so it wasn’t a gift or bribe.” You held up your hand to stop him, “Is a Mr. Dick Roman this ‘friend’? The CEO looked at you and Dean, as he hesitantly answered, “Yes”. Dean stepped closer, taking a small flask out, he grabbed the CEO’s wrist and poured some holy water on it causing it to smoke. Mr. Durcan shrieked in pain, causing a few people to glance in your direction. You turned around and smiled, “stubbed his toe, ain’t that a bitch”. Most people just smiled and went back to their conversations. You noticed a few people didn’t turn mainly, Dick, Patricia and Paul. You glared Patricia down and smiled. You heard Dean mutter something and then felt a slight commotion. You were hesitating to turn your back. “Charlie watch them, if they move tell me”. You heard Charlie say “affirmative” as you turned. Mr. Durcan was out cold, while Dean was holding him up. “As soon as I poured holy water on it, it fell on the ground and he passed out”. You discreetly looked around; luckily you were near the exit. You nodded to the door and you both inconspicuously took Mr. Durcan out. 

You searched in his pockets to find his room key. You found it and Charlie told you the number. You both started to drag him to his room. “He should recover, we can check on him in a few hours” Dean said as you continued dragging him as quietly as possible. Your struggle was interrupted by Charlie’s alarmed voice, “They are on the move and it looks like they are bringing friends”. You sigh, “How many?” You could hear Charlie typing away, “I can’t be sure but it looks like three more- a total of six unfriendlies”. You guys finally found his room, quickly opened it, and basically tossed the poor man on his bed. “We have to keep them away from this room, Charlie?” The red head spoke up, “What’s the plan?” You turned to Dean, as you spoke, “Lock all the doors in the hallways, block elevators from stopping at this floor...basically lock down this floor. Try and funnel our unwelcomed guests outside to the back recreation area.” You could already hear her typing furiously away, “Got it”. Dean nodded impressed by your plan, as he simply said, “Sam?” A few crackling noises but he finally answered, “We’re on our way. 45 seconds out”. Dean smiled as he looked at you, “Let’s go pick a fight. Shall we, princess?” You smirked and put your hand through his outstretched arm. 

You reached the recreation area basically the same time as Sam and Jo. “Damn, y/n…I have excellent taste in clothes. You two look absolutely edible.” Jo said. Dean chucked while you rolled your eyes, “Thanks but now is not the time” as you threw your partner a wink. Sam handed you a gun when Charlie said, “They’re on the move, ETA to you about 30 seconds”. You and Jo took a deep breath. Dean stepped forward, “Remember they look human but most likely the human they’re occupying is dead, just a meat suit. So, no holding back. All of you instinctively got in a circle, backs to each other that way every one had an their eyes forwards and their backs covered. 

The doors opened and three enormous unknowns walked in. You didn’t recognize these people so you weren’t sure if they were friendly or foe. One stepped forward and tilted his head, “they don’t look so tough?” as his eyes went black. Dean stepped forward and with one quick movement, the demon was done and you saw black smoke come out. The two others stormed forward launching Sam and Dean to fight. You and Jo stood back and watched them. It was almost like watching a beautiful graceful deadly dance. Your observation was cut short when the three main characters stepped forward. The gigantic lackeys were meant to distract the Winchesters as you and Jo stood head to head with Dick, Patricia and Paul. 

Paul was the first to step forward, his voice was almost two octaves lower, “Well, well what do we have here, two Winchesters and y/n. I’ve been looking forward to this”. You looked at Paul puzzled, “You’re the ring leader?” Paul stepped closer, “Surprise”. You rolled your eyes, “Seriously, come on, Patricia? Really”. Patricia didn’t move, she just stood stoically, glaring at you and Jo. “I can’t believe you’re the organizer. How anti-climatic!” you sighed. Paul laughed out loud. “I do love your feistiness y/n. I look forward to breaking your spirit later.” Jo moved closer to you. With a slight of hand, Paul threw Jo across the space, you watched helplessly as she landed in some grass. “Well, that’s new” you said, trying to get Paul’s attention. He smiled at you and stepped forward. You purposely didn’t budge, which caused him to smile more. He put his hand up and lightly touched your cheek. Dick Roman and Patricia went towards Jo who started to move a little. You turned to look at her, “Awww are you concerned about your poor little friend?” You made eye contact with Paul. Smugly smiling he said, “You should be, she’s about to die and then after we’ll find the little red head”. He gripped your face tighter and forcibly turned your head to watch his demons circle Jo. Dick leaned forward and before he could do anything, Jo side swiped him, jumped up and started swinging. Patricia started to lunge forward when a knife to the back met her; she turned around to face a pissed off Charlie. Smiling, you leaned forward, “Awww are you concerned about your poor little friends?” Paul looked around, he watched Dean kill one demon, Sam almost finishing off the other one so he decided it was time to leave. Dean immediately started to run towards you and with a flick of his wrist; Dean was thrown into the side of the building. Jo and Charlie were fighting Patricia while Sam was trying to finish off the last of the gargantuan demons. Paul gripped you in a way, that you couldn’t move at least move in a way you wanted to. “I guess this is what Dean was talking about when he said the demons can control your body.” you thought at Paul basically dragged you to a remote location. 

He took you to a room, you assumed it was his and he threw you against the floor. You stood as quickly as you could but again before you could react, he had you pinned on the bed. Despite nothing tying you down, you couldn’t move. You heard him shuffle towards the bed and then felt the bed dip down. He leaned over and gently brushed your hair away from your face. “You know y/n I’ve always liked you. You had spirit, gumption. You don’t see that a lot now a day but you had to go and ruin my sweet set up. You see I’m a crossroads demon and we basically make our way by making deals with unsuspecting human. I had the perfect set up, with a constant supply of desperate humans. I put Patricia in as CEO, make a couple bad deals and you’d be surprise how many people get real desperate real quick. Like I said, you came along and ruined a very lucrative business for me. So, naturally I have to kill you and put another one of my CEOs up there. Mr. Durcan was easy enough to control but you had to go and bring in those fucking Winchesters”. He basically growled causing you to smirk. 

He looked down at you, his expressing darkening as he leaned forward, his mouth was right by your ear as he breathed out, “I think its time, I break you your spirit”. You still couldn’t move, he took out a knife and he put it to your cheek, he began to lightly trace it down your body and then back up. “Now, where should we start?” You were desperately trying to figure out what to do but without movement capabilities you were drawing a black. His focus went back to your neck. Using the knife he brushed more of your hair away. You figured, if you could hang on long enough until they find you then you’d be ok. He lingered around your neck, smiled and nicked your neck causing you to flinch. “Now we match. You gave me a scar and now I gave you a scar.” With out warning he dug his knife down your side, splitting your dress and causing you to bleed profusely. You refused to give him any indication of pain, after all you were trained in torture techniques but you know you were going to be losing a lot of blood, if someone didn’t here fast. 

He studied your face, “I knew you’d be tough but I got to say I’m impressed. I guess physical pain doesn’t phase you so let’s move on to some emotional and physical”. You looked at him as he stood up. He removed his shoes and pants. He went to the edge of the bed and slowly crawled forward. You watched him as he began to kiss your ankles slowly moving up, “are you fucking serious, this demon was going to try and rape me?” you thought. “He is one sick demented fuck” you put your head on the pillow trying desperately to block out any sensation this demon was trying to evoke. He sat up, straddled you and leaned down putting his hands tightly around your neck strangling you. At that precise moment the door flew open, and Dean followed by Sam, Jo and Charlie rushed through. Surprised the demon lost control of your body and with one fluid motion; you pulled a knife from your garter and stabbed him in his stomach. He turned and looked at you shocked. Dean stepped forward with even a bigger knife, sliced his neck and threw him off of you. You sat back, catching your breath and sighed in relief. The bed dipped and Dean worried face was looking down at you. “How you doing princess?” he whispered. You smirked, “happy to see you, handsome”. He smiled and looked at your side. “Well, you’re bleeding pretty bad but we can stop that and stich you up. Unless you want to go to a hospital?” Bringing Dean towels, Jo answered for you. “Don’t bother, she hates hospitals. Go take care of her, we’ll clean up”. Dean looked at Sam, his brother smiled and nodded to the door. Dean didn’t hesitate and carefully he swept you up into his arms. With the towels pressed to your side, he carried you bridal style to your room. 

He gently put you on the bed and you groaned. He quickly went to your face, brushing all your hair away and anxiously trying to read your expression. You eyes were closed but you smiled at all his sweet gestures. Taking a deep breath you opened your eyes, “Well, what are you waiting for Winchester. Get to work”. He shook his head and got up to get supplies. He took scissors out and starting to cut your barely there dress, “You know when you said I could help you out of this dress later, I didn’t think you meant this way”. You laughed at him, but quickly groaned at the pain it caused. He pulled away at the fabric revealing your black lingerie and garter belt you were wearing. He took a deep breath and his eyes widen, “Damn y/n, if I knew you were wearing this under that dress, we wouldn’t have left the room” Despite your injury that comment went straight through you causing you to squirm a little. Dean didn’t miss a beat, “if that got you hot and bothered, just you wait until you’re healed.” You looked at him and smirked, “Ok, Winchester, you’re on”. A huge smile spread across Dean’s face, “lets patch you up, princess”. After about 100 stiches, Dean sighed, cleared off the bed, and tucked you into bed. He leaned down and kissed your forehead, “Get some rest sweetheart, I’m going to go check on the others”. He got up to leave when he heard you murmur, “I like sweetheart”. He chuckled, closing the door; he began to think of a ways to join him on the road.

**Notes for the Chapter:**

> Chapter 4 Complete... almost time to get it on :)
> 
> Will she stay or will she go? Hmmmm what's a girl to do?
> 
> Also, please ignore plot holes and grammatical errors, its so late by me and I wanted to escape reality for a bit. As always, thanks for reading. You guys are awesome


	5. Responsive

**Summary for the Chapter:**

> Reader gets a curious invite that changes her life

The next few days were a whirlwind. You had to create a cover story for why Patricia and friends suddenly disappeared. Luckily, Mr. Durcan’s memory was a bit hazy and he trusted you and collaborated your story. Jo and Charlie both back you up as well as your consultants. The guests of the retreat were quickly to believe the security experts and all left relieved that Patricia, Paul and Dick were no longer a threat to their company. 

In front of the civilians, you down played your injury as best you could but behind close doors, your side was aching. Dean kept checking on you but he knew with that many stiches you were out of commission for a few days. Sam got a call alerting them of a case near by. He pulled Dean aside, “We got a case, looks like a simple salt and burn and its only about two hours from here.” Dean nodded along while he watched you handle all the board members without even flitching. “She’s got to be in pain, I gave her like 100 stiches and look at her- no one knows she has a gash basically the length of her side.” Sam shook his head, “Dude, are you even listening to me?” Dean cut him off, “Yeah, yeah…salt and burn. I got it.” Sam raised his eyebrows, “Ok, so you want to take the case…” Dean finally looked at him and Sam swore he saw sadness. Quickly Sam added, “We can swing by after the case and see them…maybe even pick up some personal belongings?” Curious Dean whispered, “What are you talking about Sammy? What personal belongings?” Sam smirked, “don’t think I haven’t noticed, you like her plus she showed she could handle herself. With the right training, she would be make a badass hunter plus we’ve known her for like a week and I can tell she’s interested. Make her an offer. She’d be a great asset to the team.” Dean squinted his eyes at Sam, “go tell Charlie and Jo. I’ll go chat with y/n.” 

Dean waited to the side as you finished your last conversation. With a sigh, you turned to him and smiled. “I thought that would never end. I guess I shouldn’t underestimate the power of money”. You studied Dean’s face, “What’s up Winchester?” He smirked and stepped closer to you. “Sam and I have a case. We’ve got to go.” You looked at him, revealing no emotion but your voice gave you away, “You’re leaving now? What about?...” Dean interrupted you, “It’s only two hours away, if its all right with you, we figured we would swing by in a couple days?” You smiled slightly, “what’s the case?” Smugly smiling Dean answered, “just a simple salt and burn. Ghosts and whatnots” You bit your lip, “Ghosts, huh?” Dean started to walk towards the door. You followed after him, “You know you could call if you need help…I mean ghosts?...fascinating” Dean just watched as you began to process the information. He loved watching you think. Before you reached the door, he turned to look at you, breaking your train of thought. Looking down at you, he whispered, ‘If you ever want to get away from your ivory tower. You could always join us on the road?” You furrowed your eyebrows holding his gaze, “are you serious?” Dean simply nodded and turned. You watched him walk and quickly went after him. “Wait, just a damn minute Winchester. Are you seriously asking me to go on the road with you?” He turned, leaned down, and whispered, “Yes, I am”. He kissed your forehead, “Think about it, we’ll be back in a few days, get some rest” He winked at you and turned toward his baby. Sam stepped forward as Dean chatted with Charlie and Jo. “I assume he talked to you?” You glanced up at Sam and smiled. “He did.” Sam waited, “and?” You were silent for a moment as watched Dean talk to your friends. You looked up to Sam, “Do you guys do this a lot? Recruit people from cases?” Sam smiled, “We don’t recruit people, in fact we usually encourage people to stay away from this way of life but you’re not a civilian. You crave adventure. You’re good at your job but your not happy with it.” You stared at Sam, he read you like a book. “Plus, I know my brother and he is quite smitten with you.” Sam whispered. You blushed at Sam’s words, “Tell you what, I will really think about it. It’s definitely an intriguing offer”. Sam smiled and pulled you into a hug. You winched and he quickly let you go, “Sorry, I forgot” You laughed at him and waved him off. Jo and Charlie stood by you as you watched the impala pull out of the driveway. 

The rest of your day was spent packing up your equipment and driving back to the office. Charlie and Jo chatted mostly while you sat in the back resting but mostly thinking about Dean’s offer. “y/n, y/n?” Charlie turned and asked you, “Hey, where were you? We were talking to you?” You straightened up, “Sorry, I was just thinking” Jo looked at you through the rear view, “I know that look. Spill the beans boss.” You glared at Jo, “I got an offer and I’m mulling it over.” Charlie grinned, “I knew it. We all saw the connection.” Jo laughed, “It’s not all lovey dovey with y/n, she craves a challenge and what better challenge than fighting things that go bump in the night.” You smirked at her. 

For the first time in a long time, you took the day off; you wanted to rest and also wanted to see how Jo handled running it. You had complete faith in her, but you knew she needed to know if she could do. You lived in a small studio apartment with not much personal belongings after all you traveled for most of your adult life. You rested your side as you thought and thought and thought, dozing on and off. Your phone chimed indicating you had a message, you smirked when you saw Dean’s name. You slid the message opened and smirked, “Just checking on you, Princess. We should be by you in three days. This ghost is being a bitch”. You replied, “If you need back up, I’m only a call away”. He responded, “ It doesn’t realize I have a dress to take off.” Horny bastard you thought as you typed, “Get back to work, Winchester” 

You walked into the office the next day and met with Jo. Every thing went well, no lasting consequences from the retreat. Every thing was running smoothly, so smoothly that you decided to go home early. Before you left, Jo stopped you, “You’re planning on taking him up on his offer, aren’t you?” You looked at Jo, and simply said, “Yes”. Jo smirked, “Good, I’m beginning to like your office”. You rolled your eyes and walked to the elevator. 

The next few days flew by and before you knew it, you heard a knock at the door. Smiling, you got up to see the Winchester brothers in your doorway. You greeted Sam with a hug and then smugly smiled at Dean standing in front of him. Dean looked you up in down which you laughed considering you were wearing jeans and a tank. You shook your head and stepped into his arms, he quickly wrapped his strong arms around your waist and pulled you in tight. He noticed you didn’t wince and he wiggled his eyebrows at you, “feeling better, princess?” Rolling your eyes, you grabbed your jacket, “let’s go boys, we’re meeting Jo and Charlie”. Sam laughed and turned towards the impala. You started to walk when Dean grabbed your arm spinning you to face him. “Well, what’s the decision?” You smiled and stepped closer, “Anxious Winchester?” Dean looked at you, his eyes saying what he couldn’t. You tilted your head and nodded yes. He smiled and leaned in, his lips were warm and tasted of mint; he had obviously been chewing gum earlier. His hands wrapped around your waist and you locked yours around his neck pulling him down slightly. When you broke apart for air, you rested your forehead against his and gathered some much needed oxygen. His smirk told you everything and you smiled back, sinking into his hold. Sam beeping the horn quickly interrupted the moment, you smirked and Dean held out his hand, which you took walking hand in hand to the car. 

You met the ladies at the local bar. You all sat at a booth laughing and sharing battle stories. You stood up to get another round while Jo told yet another battle story about you. You made your way to the bar, waiting for your drinks, you turned to watch your friends. You smiled as you watched them laugh and joke. You felt the random guy come up next to you but you were hoping that he would pick up the ‘I’m not interested’ vibes you were throwing. He leaned in, before he could speak, you held up your hand, “Nope, not interested.” He groaned and you turned to get your beers. He leaned in again, “how do you know I was going to hit on you? Maybe I was asking where the bathrooms were?” You smiled at the man, pointing to the bright red restroom signs and started to walk away when he grabbed your arm. Eyes wide, you turned, “I strongly suggest you remove your hand from my arm…now”. He smiled, “Challenge accepted”. You rolled your eyes, your arms were filled with 5 beers, but before you could do anything, Dean appeared by your side .You looked down at you, “you ok, princess?” You smiled up at him; the man’s arm fell from your arm. Dean looked over at the guy, “Didn’t mean to interrupt, let me just take the beers from my girl here and I’ll let you guys finish.” You look curiously up at Dean and he raised his eyebrows, “All yours”. He took the beers from your hands and stood next to you. You walked toward the now scared man and grabbed his hand, bending it backwards, causing him to fall to his knees, you leaned in, “never grab a woman”. He nodded adamantly as he said sorry over and over again. You let his hand go and watched him run off. You turned to Dean as he handed you a beer, “that’s my girl” as he kissed your cheek. 

You two sat in the booth only to be greeted by Jo, Charlie and Sam looking at you. Jo laughed, “We can’t take you anywhere, y/n” You laughed, “He started it” pointing to Dean. Charlie looked at Sam, “Are you sure you handle both of them?” Sam started to laugh, “I know who to call for back up”. The rest of the night was fun and relaxing. A perfect send off. Last call and you guys got up to leave. Sam started walking with Charlie and Jo when you and Dean stopped. “Sam, Where are you going?” Dean asked. Jo started to laugh, when Sam stopped short, “There’s no way in hell, I’m going to spend the night in a studio apartment with the two of you going at it like rabbits.” You mouth fell opened as Jo and Charlie burst out laughing. Dean looked at you and smirked, “hey, who says she is getting anything tonight. Maybe I’m tired” Dean said completely serious. You turned and looked at him as he smirked. Grabbing your hand, he started walked you two to the impala, walking away from the laughter of Jo, Charlie and Sam. 

You pulled up to your apartment and both got out. You didn’t really talk much, just walked towards the door. As soon as you opened the door, Dean wrapped his arms around you. “Thought you were tired, Winchester?” you said smirking. Dean turned you around, “I don’t think I could ever tire of you”. You smiled as he leans in and kisses you passionately. Every part of you lights up. Suddenly his hands are everywhere and you wrap your legs around him. He presses you in to the wall, and you let out a soft moan, you feel him began to hardened and you rock your hips forward. He groans as he attacks your neck, kissing, biting and sucking. You were a moaning mumbling mess, gripping his back, and pressing your bodies closer and closer. Dean moved you away from the wall, stumbling towards your bed; you both stopped at the foot of it, looking at each other. Dean brushed your hair away, “You know we don’t have to do this. We will have plenty of time on the road”. You studied his face, such a strong man but also so considerate. You fumbled with the hem of your tank, smirking, you pulled it over your head revealing your black lace bra. Dean’s eyes went right to it and practically growled. Looking back at you, he smiled and leaned in and kissed you, his hands were all over your back, going down towards your ass. He squeezed your ass causing you to moan in his mouth, he broke away from your lips, and travelled down your neck towards your breasts. You felt his hands on your back fiddle with your bra clasp. With expertise, he unhooked it, causing your breasts to spring free, he groaned as he quickly moved his mouth to your nipples. You back automatically arched forward, you felt Dean grin as he continued to massage and suck on your breasts. “Dean, I want you to look how ready I am, don’t you want to put your dick in there?” Dean’s mouth fell opened as he dropped to his knees, he unbutton your jeans and slid them down, smirking at your little black thong, he looked up again and you nodded as he slid your thong down. He stood up and you immediately took his shirt off, “Too many damn clothes, Winchester”. “Yes ma’am” he said as he began to strip his layers, he gently pushed you on the bed, gripping his cock and gently stroking it. He looked at you, “now, spread your legs wide for me, princess. Your body is mine tonight”. You slowly spread your legs as he inched closer and closer over you. He kisses you fervently, running his hands up your body. He moves his mouth to your neck, continuing to mark his territory. “Dean, Dean” you mange to breath out, he looks at you, “Dean, fill me up, I need you to fuck my tight cunt! Make me scream with that big dick of yours”. You feel his cock twitch at your words and he drops his head into your neck, “Damn Princess”. He positions himself and slides right in causing you to moan his name. You both wait a second to adjust before you look at him and smile, “Fuck me, right now”. Dean groans, “As you wish, princess” and he slams into you over and over again, hitting your spot relentlessly. You were a moaning squirming mess, “so close, Dean, so close”. He kept at it as he said, “Come with me y/n.” He slammed into you hitting you perfectly that you let out a scream. He grunted a few times, as he came right after you. Breathing heavily, he slid out, causing you to groan already missing him being inside you. He looks at you and smiled, “Damn baby, I love that filthy mouth of yours”. You smiled and leaned your head back against the pillow. Breathing heavily, “That was some great sex, Winchester”. He got up to get a towel and kissed you on the forehead, “Oh baby, that was only round one”.

 

The next morning, Sam, Charlie and Jo called to meet at a diner. As you and Dean walked in, Charlie laughed, “I think you made the right decision staying with us”. Sam and Jo looked at you and Dean. Jo smirked, “Did you sleep at all?” Dean grinned, “Sleeps overrated” as he kissed your cheek. You all sat down and ate. Saying goodbye to Jo and Charlie was harder than you expected but they each promised to call and visit. You knew that you would be seeing them soon so you said your goodbyes and climbed into the back of the impala. Dean managed to hit your ass as you climbed in. Sam just groaned, “Do I need to talk to you two about PDA?” You laughed and leaned forward, kissing Dean on the cheek. “Where to boss?”

**Author's Note:**

> Just something I thought of. Thanks for taking the time to read:)


End file.
